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This compound’s heptanitro- derivative may be a more potent explosive than octogen. For 10 points each:
[10h] Name this compound first synthesized in 1964 by Philip Eaton and Thomas Cole, whose structure was once thought to be impossible. This compound’s highly-strained sp3 carbons make it useful for energy-storage purposes.
ANSWER: cubane
[10e] Cubane has been investigated as a bioisostere for this compound in drugs like lumacaftor, since cubane groups are often more soluble and don’t get oxidized by cytochromes p450. This aromatic hydrocarbon has formula C6H6.
ANSWER: benzene
[10m] Two answers required. Part of the difficulty with using cubane as a benzene bioisostere is that it’s very hard to synthesize 1,3 (“one-three”) and 1,2- (“one-two”) disubstituted cubanes, which correspond to substitutions at these two benzene positions. These two substitution positions on benzene are closest to the original substituent.
ANSWER: ortho AND meta [or O AND M]
<JF, Chemistry>

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